AlCl3-promoted highly regio- and diastereoselective [3 + 2] cycloadditions of activated cyclopropanes and aromatic aldehydes: Construction of 2,5-diaryl-3,3,4-trisubstituted tetrahydrofurans

Journal of Organic Chemistry

Volumn 76, Issue 1, 2011, Pages 229-233

  Yang, Gaosheng ^a   Shen, Yue ^a   Li, Kui ^a   Sun, Yongxian ^a   Hua, Yuanyuan ^a  

^a ANHUI NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDE; ARYL ALDEHYDES; CYCLOADDITION REACTION; CYCLOADDITIONS; DIASTEREOSELECTIVE; DIASTEREOSELECTIVITIES; DICARBOXYLATES; ELECTRON-RICH; GOOD YIELD; TETRAHYDROFURANS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

ALDEHYDES; AROMATIC COMPOUNDS; CYCLOADDITION; PROPANE; STEREOSELECTIVITY;

CARBOXYLATION;

ALDEHYDE DERIVATIVE; ALUMINUM CHLORIDE; CYCLOPROPANE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; ALDEHYDE; ALUMINUM DERIVATIVE; CHLORIDE; FURAN DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

ALDEHYDES; ALUMINUM COMPOUNDS; CATALYSIS; CHLORIDES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOPROPANES; FURANS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 78650890753     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1020773     Document Type: Article

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30. See the Supporting Information. The crystal structures have been deposited with the Cambridge Crystallographic Data Centre; deposition nos. CCDC 795516, 795517, 795518, and 795519 for 3aa, 4aa, 5aa, and 6a, respectively. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/ conts/retrieving.html.
31. See the Supporting Information. The crystal structures have been deposited with the Cambridge Crystallographic Data Centre; deposition numbers: CCDC 795520 and 795521 for 3ac and 4ag, respectively. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html.
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34. 1H NMR analyses (4 h, >90% conversion). For detailed information see the Supporting Information (S58-S59).
35. We thank one of the reviewers for proposing this mechanism.